Softening agent for cotton and for synthetic textile substrates

ABSTRACT

A process for the production of an alkali metal salt of sulfated monoolefinate ester of a polyalkylene poly hydroxy-alcohol-type compound.

United States Patent [191 Brown 1 Apr. 3,1973

[54] SOFTENING AGENT FOR COTTON [56] References Cited AND FOR SYNTHETIC TEXTILE SUBSTRATES UNITED STATES PATENTS 75 Inventor; James Marvin Brown, Charlotte 3,383,396 5/l968 Cahn et al. ..260/400 NC 2,743,288 4/1956 Rueggeberg et al ..260/400 3,385,873 5/1968 Caldwell ..260/400 [73] Assignee: American Cyanamid Company,

Stamford, Conn. FOREIGN PATENTS OR APPLICATIONS [22] Filed: Mar. 9, 1970 8,526 6/1956 Japan ..260/400 [21] Appl' 17868 Primary Examiner-Elbert L. Roberts Related U.S. Application Data Attorney-Charles J. Fickey [62] Ser. No. 583,976, Oct. 3, I966, Pat. No. ABSTRACT A process for the production of an alkali metal salt of U-S- I i sulfated monoolefinate ester of a polyalkylene [51] Int. Cl. ..C07c 143/90, C1 id 1/28 hydroxy alcohol type compound [58] Field of Search ..260/400 1 Claim, N0 Drawings SOFTENING AGENT FORCOTTON AND FOR SYNTHETIC TEXT ILESUBSTRATES This is a divisional application ofa copending application, Ser. No. 583,976, filed-Oct. 3, 1966. now US.

' Pat. No. 3,509,048

Heretofore, a major problem encountered in the employment of textile softeners-for cellulosic fabrics has been the lack of stability of the softener'composition to metallic ions while concurrently retaining'theproperties of good rewettability andsoftening. For example, as a result of this prior poorstability-'ofvarious softening agents, it has not been possible to use a finishing softener 'for cellulosiefabrics previously resin-treated.-

As a typical example'of the lack of stabilityofsome of the prior softening compositions, whenaprior'composition is placed at about 6 percent by'weight inan aqueous solution containing aboutl percent of sodium bisulfite and not morethan about 1 percent magnesium chloride, such a test indicates that'the higher percentages of sulfated fatty-acid sodium=salt.cause'the softening composition to-be much lesssuitableefor obtaining a good and desirable textile finish, whereas when the sulfated fatty-acid sodium saltis'employed in smaller percentages, a markedlack of stability of'thesoftenin'g composition results.

Accordingly, it is an object of this invention toproduce a softening composition suitableforthe treatment of cellulosic textiles.

Another object is to produce a softening'composition stable to metallic ions and characterizedby the properties of good rewettability and softening.

Another object is to obtain a cellulosic fabric impregnated with the abovecomposition.

Another object is to obtain a process for the production of the above cellulosic composition.

Other objects become apparentfrom the above and following disclosure.

The objects of this invention are obtained by the employment of an alkali salt of sulfated mono-olefinate ester of a polyalkylene polyhydroxy-alcohol-type compound. The preferred alkali metal is sodium, the preferred olefinate ester'is ofoleicacid, and the polyalkylene polyhydroxy-alcohol-type compound preferred for the invention is diethylene glycol.

The alkali salt of the sulfated mon'o-olefinate-ester of a diethylene glycol-type compound is employed in a conventional manner to impregnate a cellulosic textile material such as cotton to obtain the novel impregnated cellulosic material of this invention.

The alkali salt of sulfated mono-olefinate ester of a diethylene glycol-type compound is formed by ,a process comprising (1) reacting an olefinic acid with diethylene glycol-type compound sufficiently to form substantially a major amount of mono-olefinateester of polyalkylene polyhydroxy-alcohol-type compound, (2) sulfating said ester comprising reacting said ester with fuming sulfuric acid sufficiently to form substantially a major amount of sulfated mono-olefinate ester of polyalkylene polyhydroxy-alcoholtypecompound, and (3) reacting (a) said sulfated mono-olefinate ester of poly-alkylene polyhydroxy-alcohol-type compound with (b) an alkali metal hydroxide sufficiently to form the alkali metal salt of said ester.

The advantages made possible by the softening com- 5 position of this invention is a combination of advantages heretofore not possible with softeners of the prior art. By the employment of the invention as described above, it is possible to obtain a stable finish and to concurrently obtain a treated textile cellulosic material such as a textile fiber or fabric thereof which is characterized by a desirable softness of hand and the property ofgood rewettability. The advantages of this invention are particularly applicable to materials such as denim and toweling.

The polyalkylene polyhydroxy-alcohol-type compound of this invention may be derived from any of the olefineacids typicallyrepresented bythe formula C l-I COOH, such as acrylic acid, buten'ic acid, pentenic acid, hexenic acid, teracrylic acid, hypogaeic acid, oleic acid, erucic acid,and the like.

The ester-portion of thepolyalkylene polyhydroxyalcohol-type compound of this invention refers to the ester of any polyalkylene glycol which ester is eater soluble and which polyalkylene glycol is derived from alkylene oxides or glycols, such as those typically represented by the formula HO(C 1 H, 1 O) 2 H, in whichsn is an integer from 2 to about 8 and in which n is an integer from about to about 450. It is not necessary that all the alkylene radicals present necessarily be the same; i.e., polygly cols containing a mixture of alkylene radicals can be used, including ethylene, propylene, trimethylene, tetramethylene, and the like radicals.

Although it should be noted that it is critical to this invention that the olefinate ester be a monoolefinate, as contrasted to a di-olefinate" ester, it is within the scope of this invention to employ the functionally equivalent derivatives of olefinic acid, and of a polyalkylene poly-hydroxy-alcohol-type compound, provided that the advantages of the invention are not negated'by the employment of such a derivative.

The applicationof the novel product or composition ofthe product of this invention to a cellulosic material such as a textile fabric is carried out by any standard or conventional processing technique, such as dipping, exhaustion, padding, spraying, and the like. Although water is a conventional solvent normally employed in the application of the composition of this invention to a cellulosic material, such as a textile fabric, it is within the scope of the invention also to employ alone or in a compatiable mixture, any one or more solvents such as acetone, dimethyl formamide, benzene, tetrahydrofuran, toluene, xylene, and the like; but it is alsocontemplated that emulsions may be employed. The chlorinated hydrocarbons such as ethylene dichloride, tetrachloroethane, and carbon tetrachloride are other typical examples of a suitable vehicle. In order to obtain the benefits of this invention for a cellulosic material impregnated with the softener of this invention, it is necessary only that the material be impregnated sufficiently to obtain the desired properties described above. However, normally it is necessary that the alkali salt of sulfated mono-olefinate ester of a polyalkylene polyhydroxy-alcohol-type compound be employed in an amount sufficient to obtain from about 0.25 percent up to about 2 percent solids on the weight of the fabric (material) after drying. However, it should be noted that the amount of the novel softening composition of this invention required will depend largely on the use for which the impregnated cellulosic material is to be utilized, and also it will depend upon whether the impregnation is prior to, or alternatively sub.- sequent to, the employment of one or more resins in the treatment of the cellulosic material and the nature of the resin, as well as the presence and nature of any one or more catalysts.

The following example is solely for the purpose of illustrating the invention and does not limit the invention except in so far as the invention is limited and the appended claims.

EXAMPLE To a glass-lined reactor charge 3626 lbs. diethylene glycol, 9,675 lbs. oleic acid and 1 1 lbs. para-toluenesulfonic acid.

Heat batch to a maximum temperature of 185C. allowing temperature to rise as reaction proceeds. Apply vacuum as water-of-reaction distilliation rate slackens.

React under vacuum to an acid number of 11 maximum.

Vent vacuum with inert gas and cool batch to 35-40 C. for pump-out. Batch size of ester will be approximately 12,600 lbs.

Pump to lead-lined sulfator and cool to 15C. 6,300 lbs. of the mono-oleate ester.

With agitation, add slowly, maintaining temperature of the batch at 15 20C., 2,520 lbs. 98 percent fuming sulfuric acid with 20 percent free sulfur trioxide.

When the sulfuric acid is all added to the mono-ester, allow to stir at 15 20C. until the titration of a gm. sample is 45 55 ml. 05N NaOH to a methyl orange end-point. v

Meanwhile, charge to a lead-lined wash tank approximately 1,100 lbs. water and 2,400 lbs. 24 percent sodium hydroxide.

When the sulfated ester is in specification, add to sodium hydroxide solution with agitation, keeping the temperature below 80C. 1

Adjust batch to a titration of 1.0 ml. 0.5N Hcl per gm. sample to methyl orange.

Turn off stirrer and let batch separate at 60-80C. until two clear layers are obtained.

Drain the bottom layer to the sewer (sodium sulfate solution). 1

Turn on stirrer and blend material in kettle until uniform, while cooling to 40C.

Adjust batch to 59 61 percent water and 0.5 0.6 percenttotal alkalinity.

It is understood that the above disclosure is intended to include all functional equivalents thereof for compounds and processes which would be obvious to a person of ordinary skill from the above disclosure, and that the invention disclosed herein is limited only to the extent of the appended claims.

I claim:

1. A process for producing the alkali metal salt of sulfated mono-olefinate ester of diethylene glycol which comprises:

reacting oleic acid with diethylene glycol sufficiently to form substantially a major amount of monoolefinate ester of polyalkylene polyhydroxy-alcohol-type compound, in which the oleic acid is reacted in an amount of about 1 mole with about 1 mole of diethylene glycol, in which the reaction takes place in intimate contact with at least a minor amount of para-toluene sulfonic acid, in which the esterification reaction is carried on substantially during agitation of the oleic acid and the diethylene glycol, in which the esterification reaction is carried on substantially at elevated temperatures up to not more than about C., in which the esterification reaction during final stages of the esterification reaction is subjected to substantially a vacuum and substantially concurrently is reacted sufficiently to obtain an acid number of not more than about eleven, in which thereafter a reaction product of the esterification reaction is vented and is cooled to from'about 35C. to about 40C., and subsequently to from about 10C. to about 20C., in which the sulfating reaction employes about 98 percent fuming sulfuric acid having at least about 20 percent free sulfurtrioxide, in which the fuming sulfuric acid is employed at about 35 percent to about 45 percent by weight of mono-oleate, in which agitation is employed substantially throughout the sulfating reaction while substantially concurrently a reaction temperature is maintained at about 15C. to about 20C., in which the sulfuric acid is added and reacted to a point at which a 5 gram sample requires about 45 55 ml. 0.5N NaOH to obtain a methyl-orange end-point, in which the alkali metal hydroxide comprises sodium hydroxide, in which the reaction with sodium hydroxide is carried out sufficiently to form a sodium salt of .the sulfated ester, and in which a final reaction mixture comprising the sodium salt of the sulfated ester is adjusted to a titration-methyl-orange end-point of about 0.5 1.5 ml. 0.5N HCl per 10 grams ofthe final product.

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